Starting at $5,995 per person
7 Days, 6 Nights, November 15-21, 2025
Islands and island nations all over the world have always captivated people with their unique combination of isolation and connection. Perhaps none more so than Cuba. On this journey, you will delve into a rich and fascinating narrative—a complex tapestry woven by European explorers; enslaved Africans; and Indigenous Taíno people who converged on the island in the 16th century, leaving a lasting imprint on its heritage. Its architecture, food, music, and culture all reflect this rich history. Led by The Great Courses professor Joyce Salisbury, you will explore Cuba’s complicated historical, political, and economic past to gain insights into its present trajectory. By engaging with the entrepreneurial spirit of the next generation in Cuba; contemplating the world-renowned rhythms of Cuban music deeply rooted in West African culture; and visiting historic sites like Playa Girón, the site of the Bay of Pigs invasion, you will begin to peel back the layers of Cuba’s story. Through the expertise of Dr. Salisbury, you will connect with Cuba’s past and gain a profound understanding of its heritage and ongoing evolution in the global landscape.
Embark on a tour of Playa Girón and the Bay of Pigs Museum, delving into the pivotal history between the United States and Cuba, and lasting impact of the embargo.
Exchange in meaningful discussion with entrepreneurs on what they see as the economic future of Havana.
Participate in morning discussions with Dr. Joyce Salisbury about the thematic focus of each day’s activities.
Immerse yourself in Havana’s rhythms during a rooftop jam session, a salsa or Afro-Cuban percussion lesson, and a youth jazz/funk band.
Explore Cuba’s Indigenous and Afro-Cuban roots through visits to the Museum of Archaeology and the vibrant neighborhood of Callejón de Hamel.
Joyce E. Salisbury is Professor Emerita of Humanistic Studies at the University of Wisconsin–Green Bay, where she taught history and served as associate dean of Liberal Arts and Sciences and director of International Education. She earned her PhD in Medieval History at Rutgers University, specializing in religious and social history.
Dr. Salisbury began her career conducting research in Spain. She continues to travel there to conduct further research, lecture, and guide students and other travelers. She has produced several Great Courses, the first of which was The History of Spain: Land on a Crossroad. She has recently completed a new Great Course on the Mediterranean world.
In addition to receiving the University of Wisconsin’s Outstanding Teaching award, she was named Professor of the Year in 1991 by the Council for Advancement and Support of Education. She has taught three times during the study abroad program, Semester at Sea, on a ship that circumnavigates the world with more than 500 students for a full semester.
Arrive at José Martí International Airport and transfer to your boutique hotel in Havana’s centrally located Miramar neighborhood. Begin your journey with an orientation meeting and welcome lecture by your tour expert, Dr. Joyce Salisbury, who will delve into the themes of the week. Experience Havana’s charm firsthand with a driving tour along the famed seawall and through the Vedado neighborhood as you cruise in 1950s cars, an iconic symbol of the complex relationship between the United States and Cuba. As the sun sets, toast the beginning of your adventure with a rooftop jam session featuring local musicians. Then dine at El Cocinero, a stylish restaurant housed in a former factory overlooking the Almendares River. If you wish to extend your evening, explore multimedia gallery spaces and experience a live performance at Fabrica de Arte Cubano.
Included Meal: Dinner
Accommodations: Casa Italia
Each morning, start your day with a 30-minute informal chat led by Dr. Salisbury, focusing on a theme that will shape your day’s activities. Today’s focus will be Cuba’s Indigenous roots from Taíno culture to Afro-Cuban influence. Engage in a conversation with a local historian and former director of the Cultural Patrimony Section at the City Historian Office. Explore Cuba’s rich history with a visit to the Museum of Archaeology, guided by a local expert who will illuminate the lives of Cuba’s Indigenous inhabitants. Afterward, take a leisurely walking tour en route to a traditional Cuban lunch at a paladar (a privately run restaurant) offering authentic local cuisine. Immerse yourself in Havana’s vibrant culture and Afro-Cuban history at Callejón de Hamel, where you can witness a live rumba performance in a neighborhood known for its cultural heritage. Later in the afternoon, choose from various activities such as experiencing a local folk dancing group or participating in a hands-on dance lesson or drumming class. Conclude your day with dinner at one of Cuba’s pioneering female-led paladars, housed in a historic former residence.
Included Meals: Breakfast, Lunch, Dinner
Accommodations: Casa Italia
Gather with Dr. Salisbury this morning as she explores the theme of isolationism. Throughout the day, gain profound insights into Havana’s cultural, political, and socioeconomic landscape as you meet with Cuba’s top urban planner and discuss the city’s evolution against the backdrop of its history and current influences. Embark on a journey through Havana’s iconic landmarks such as Morro Castle, La Cabaña, and Revolution Square, reflecting with Dr. Salisbury on Cuba’s history of invasions and the impact on later isolationism. Enjoy a leisurely lunch at a leading paladar in the slow-food movement, savoring authentic Cuban cuisine. Visit the historic Hotel Nacional de Cuba, a monument to the economic heyday of Havana in the late 1940s when the Mafia used it for the Havana Conference to discuss important rules and business. At a private class, delve into Cuban cigar craftsmanship with a local expert.
Included Meals: Breakfast, Lunch
Accommodations: Casa Italia
Meet with Dr. Salisbury this morning as she discusses Cuba’s current economic inflection point and starts to peel back the layers of how the U.S. embargo has affected Cuba’s economy for almost 65 years. Embark on a fascinating day starting with a tour of Finca Vigía, Ernest Hemingway’s former residence where his extensive book collection and beloved boat, El Pilar , are still preserved. Engage in a thought-provoking panel discussion with Cuban entrepreneurs and economist Oniel Díaz, exploring emerging opportunities in the private sector. Enjoy a unique dining experience onsite with these entrepreneurs, accompanied by a private musical performance by Primera Linea, a youth band blending New Orleans and Cuban music. Later in the day, choose between a salsa-dancing session or an Afro-Cuban percussion class to further immerse yourself in Cuban culture. As you prepare to leave Havana for Playa Girón, join a veteran for a firsthand account of the historic 1961 Bay of Pigs invasion, gaining deeper insights into this pivotal event.
Included Meals: Breakfast, Lunch
Accommodations: Casa Italia
Embark on a full day’s journey beginning with a southward drive of approximately 2.5 hours to the Ciénaga de Zapata, a UNESCO Biosphere Reserve, and one of the largest and most diverse in Cuba. Then tour Playa Girón and the Bay of Pigs Museum to immerse yourself into the place that sparked and shaped so much of current U.S.-Cuban relations. A picnic lunch will be provided as you soak in the history of the picturesque beach before continuing your journey, approximately 2 hours, to Trinidad in central Cuba, renowned for its charming cobblestone streets, pastel-colored homes, and inviting small-town atmosphere. Upon arrival, settle into your casa particular (private rental house) before joining a walking tour led by a local architect, historian, and restoration specialist to explore Trinidad’s rich architectural heritage. Conclude the day with a home-cooked meal prepared by your hosts.
Included Meals: Breakfast, Lunch, Dinner
Accommodations: Hostal Lola or similar casa particular
Continue your exploration of Cuba’s rich history with Dr. Salisbury leading a final discussion on the role of sugar in shaping the island’s cultural, political, and economic landscapes. Journey to the archaeological site of San Isidro near Trinidad to delve into the history of Cuba’s sugar cane industry during the 18th and 19th centuries. Enjoy a farm-fresh lunch in the scenic Sugar Mill Valley before returning to Trinidad for an afternoon of leisure, perfect for exploring local markets and museums at your own pace. Conclude your Cuban adventure with a farewell dinner and live musical performance in Trinidad’s historic center, celebrating the culmination of your journey.
Included Meals: Breakfast, Lunch, Dinner
Accommodations: Hostal Lola or similar casa particular
Depart from Trinidad this morning, making a poignant stop en route to the airport at the Che Guevara Memorial and Museum. Here, you’ll encounter the final resting place of Marxist revolutionary Ernesto “Che” Guevara. Reflect on the legacy of Che Guevara before proceeding to Santa Clara International Airport for your individual flight back to the United States.
Included Meals: Breakfast
After breakfast at the hotel, transfer to the airport independently for your flight home.
Included Meals: Breakfast
Please note: Much of the infrastructure in Cuba has not been updated to meet accessibility standards and can be challenging for those with mobility issues, including balance issues, using a cane/mobility aid, or walking challenges. The sidewalks and streets are in poor condition, and it is difficult to maintain an uninterrupted flat surface for any stretch of distance. Almost all restaurants and several visits require climbing at least two to three flights of stairs to access. All stairs have handrails on at least one side, but many staircases are narrow, and some are winding. Travelers will need to be able to climb up and down these stairs without assistance. There are no elevators.
Hostal Lola (or similar)
Casas particulares are privately (not government) owned hotels throughout Cuba where American citizens are legally authorized to stay. They are often former colonial mansions restored into about 7 to 10 rooms and professionally operated. Expect spare but clean rooms, air conditioning, private bathrooms, and warm hospitality. Full groups will often be split among two to three nearby casas of similar quality.
Originally a colonial mansion, this privately owned boutique hotel offers an elegant refuge in Havana. The hotel’s 19 meticulously designed rooms offer character, comfort, and luxury. Centrally located on a quiet, beautiful street in the Miramar neighborhood, the hotel is surrounded by striking architecture and public spaces. The property features an on-site Italian restaurant.
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